Position Summary

Tipalti's Commercial Legal Team is adding a Senior Commercial Counsel to its Toronto office. You'll be heavily relied on by a tight, high-autonomy team that treats AI as infrastructure, not novelty. Your practice will span both sides of the commercial deal sheet, and your influence will extend well beyond contract negotiation into how this team operates and evolves. This role reports to the Director, Commercial, within a team of three. You'll get structured ramp-up time, the tools and training you need to operate at full speed, and the support to build real confidence in Tipalti's products, business, and regulatory landscape before we turn up the volume. Why join Tipalti? Tipalti is the AI-powered platform for finance automation, elevating how finance teams operate in the global economy. We empower our customers to scale faster and smarter by removing the complexities of doing global business and accelerating their finance operations efficiency. Our platform provides a comprehensive suite of finance automation solutions designed for mid-market businesses across accounts payable, global payouts, procurement, employee expenses, corporate cards, supplier management, tax compliance, and treasury. Tipalti partners with leading financial institutions such as Citi, Wells Fargo, J.P. Morgan, and Visa, enabling over 5,000 global companies to efficiently and securely pay millions of suppliers and payees across 200+ countries and territories, in 120 currencies. At Tipalti, we pride ourselves on our collaborative culture, the quality of our product and the capabilities of our people. Tipaltians are passionate about the work they do, and keen to get the job done. Tipalti offers competitive benefits, a flexible workplace, career coaching, and an environment where diverse individuals can thrive and make an impact. Our culture ensures everyone checks their egos at the door and stands ready to reach for success together. Founded in Israel in 2010, Tipalti is a global business headquartered in the San Francisco Bay Area (Foster City) with offices in Tel Aviv, Plano, Toronto, Vancouver, London, Amsterdam, Tbilisi and Medellin.

In this role, you will be responsible for

Own the Sales-Side Pipeline. You'll negotiate and close the Tipalti Services Agreement, along with order forms, schedules, SOWs, partner and alliance agreements, and channel deals. You'll handle security questionnaire escalations, privacy and DPA negotiations, and commercial and contractual inquiries from sophisticated international buyers, managing each from first markup to signature with minimal oversight. Drive Vendor-Side Contracting. You'll lead commercial contracting of Tipalti's vendor engagements, coordinating risk reviews with internal teams. Software agreements are the bread and butter, but you'll also handle accounting, professional services, marketing, consulting, events, and other operational agreements. You'll participate in vendor due diligence and the procurement-led intake process while coaching the procurement team and other teams on contracting processes and workflow improvements. Advise the Business Directly. You'll be a primary commercial legal point of contact for stakeholders across sales, customer success, procurement, finance, marketing, security, and go-to-market teams in every time zone Tipalti operates in. Customer retention, dispute resolution, commercial regulatory and compliance: you'll field these and drive them to resolution. Shape the Contracting Playbook. You'll help reengineer how the commercial legal team operates, from templatizing agreements to building AI-powered workflows. Within your first quarter, you'll own key segments of the contracting pipeline and begin contributing to the team's AI integration roadmap. Use AI Like a Boss. You'll calibrate its use to the risk profile and complexity of each matter, applying professional judgment to every output. We need someone who already uses AI, understands its limitations, and knows how to right-size it across contract types. Run Your Own Book. You'll carry a full portfolio of matters and exercise independent judgment on risk, deal structure, and escalation. You'll communicate directly with opposing counsel, business leaders, and cross-functional partners, handling matters from intake to close.

About you

You hold a common-law law degree (J.D., LL.B., or equivalent) and are in good standing with the Law Society of Ontario. We are open to other Canadian jurisdictions or US-qualified counsel. You have 8+ years in commercial technology transactions, ideally with both law firm and in-house software company experience. SaaS agreements, DPAs, NDAs, SOWs, and partner agreements are second nature. You are genuinely enthusiastic about AI tools and legal technology, and your willingness to teach others matches your own skill. You communicate directly and collaboratively, and you're built for a team that stays tightly connected. Your judgment on sensitive matters is independent, your attention to detail is sharp, and your comfort managing volume in a fast-moving environment is proven.

Our benefits package includes

Hybrid working model that requires you to be in office Monday, Tuesday, and Thursday Competitive salary and equity Matching RRSP Extended benefits, Employee Assistance Program, life insurance, AD&D, LTD Maternity, Paternity and Fertility Treatment benefits 15 days of PTO Subsidized lunch on office days Fresh fruit, snacks & drinks in office Conveniently located close to transit Phone/internet allowance Regular company-wide social events Multiple ERG groups celebrating our diversity and creating an inclusive culture Base Salary Range: $147,000 - $183,000 CAD annually. The compensation information, above, reflects our reasonable expectation for this role based on several factors, including current market conditions. Final compensation will be determined through individual assessment of experience, skills, qualifications, and other job-relevant factors. Actual offers may vary within or, only in exceptional circumstances, outside the stated range based on the candidate's unique qualifications and our comprehensive evaluation process. We are committed to equitable compensation practices in compliance with applicable employment laws. #LI-Hybrid Our Mission Our mission is to elevate how finance teams operate in the global economy. We empower our customers to scale faster and smarter by removing the complexities of doing global business and accelerating their finance operations efficiency. We are the AI-powered platform that automates finance. Tipalti is fueled by a commitment to our customers and a desire to build lasting connections. Our client portfolio includes high-velocity businesses such as Amazon Twitch, GoDaddy, Roku, WordPress.com, and ZipRecruiter. We work hard for our 99% customer retention rate which is built on trust, reliability and innovation. Tipalti means we handled it" - a mission to which we are constantly committed.

Accommodations

Tipalti champions inclusive teams, in which every voice counts. We are committed to recruiting diverse candidates with varied personal experiences and abilities. We welcome applications from candidates belonging to historically underrepresented or disadvantaged groups, and maintain an equitable Talent Acquisition process that is free from discrimination. As an equal opportunities employer, Tipalti complies with employment and human rights laws across the various jurisdictions in which we operate. Should you require reasonable adjustments or accommodations during the recruitment process, including access to alternate formats of materials, meeting spaces, or other accommodations that could better enable your full participation, please reach out to hr@tipalti.com for assistance.

AI Use

We may use artificial intelligence and automated systems (collectively "AI") to screen, assess, and select candidates during our recruitment process. This includes resume screening, skills assessment, and candidate matching. You have the right to request human review of any automated decision. For more information about how we collect and use personal data and information during recruitment, please refer to our Job Candidate Privacy Notice. For additional questions about our use of AI during our recruitment process, you can contact hr@tipalti.com.

Privacy

We are committed to protecting the privacy interests of job applicants and candidates. For more information about our privacy practices during our Talent Acquisition process, please refer to our Job Candidate Privacy Notice below: Job Candidate Privacy Notice | Tipalti www.tipalti.com/privacy/job-candidate-privacy-notice/